Ethyl Acetate → 5-Bromo-4-cyclopropyl-1(3H)-isobenzofuranone

HRID 1501828Notes

Reaction equation

HRID 1501828 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH:12]=[CH2:13].[CH3:14]COC(C)=O>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH:12]1[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 66643955HCID 66643955, compound

Product 1

HCID 666439405-Bromo-4-cyclopropyl-1(3H)-isobenzofuranone

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a cooled (0° C.) mixture of 5-bromo-4-vinyl-2-benzofuran-1(3H)-one (2.2 g, 9.21 mol) and Pd(OAc)2 (100 mg) in EtOAc (50 mL) was added a solution of CH2N2 in ether (100 mL) slowly. The resulting mixture was stirred at room temperature overnight, then quenched with acetic acid, filtered and the filtrate washed with water and brine, dried and concentrated to provide title compound.

Workup

  1. temperatureTo a cooled
  2. customquenched with acetic acid
  3. filtrationfiltered
  4. washthe filtrate washed with water and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b730c34c689a4a59b3515a08270daa8d
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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